Process for producing laurolactam

Abstract

Provided is a process for efficiently producing laurolactam by simple steps from cyclododecanone and hydroxylamine. This production process comprises the steps of: (a) reacting cyclododecanone with hydroxylamine in an aqueous solution in the presence of an oxime-formation solvent to produce cyclododecanone oxime; (b) separating the reaction mixture obtained after the oxime-forming step into an oil and an aqueous phases and collecting a solution of cyclododecanone oxime of the oil phase; (c) removing a part or all of the oxime-formation solvent and dissolved water from the solution of cyclododecanone oxime which is collected as an oil phase in the oil / aqueous phase separation step, whereby preparing a solution containing a rearrangement solvent to be used in a rearrangement reaction in a later step and the cyclododecanone oxime; (d) producing laurolactam from cyclododecanone oxime by rearrangement reaction using an aromatic-ring containing compound as a rearrangement catalyst; and (e) separating and removing the rearrangement solvent and the rearrangement catalyst from the reaction mixture after the rearrangement step, and purifying the laurolactam.

Description

[0001]This application is the U.S. National Phase under 35 U.S.C. §371 of International Application PCT / JP2008 / 071044, filed Nov. 19, 2008 designating the U.S., and published in Japanese as WO2009 / 069522 on Jun. 4, 2009, which claims priority to Japanese Patent Application No. 2007-308746, filed Nov. 29, 2007.TECHNICAL FIELD[0002]The present invention relates to a process for producing laurolactam from cyclododecanone and hydroxylamine by an industrially convenient process.BACKGROUND ART[0003]A common industrial process for producing an amide compound involves Beckmann rearrangement of a corresponding oxime compound. For example, ε-caprolactam which is industrially useful is produced by Beckmann rearrangement of cyclohexanone oxime. Rearrangement catalysts used are generally concentrated sulfuric acid and oleum. Since these strong acids must be used in the stoichiometric amounts or more, they form a large amount of ammonium sulfate as a byproduct during neutralization. Although laur...

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Benefits of technology

[0036]Since the present invention does not employ concentrated sulfuric acid or oleum, byproducts such as ammonium sulfate are not produced, and the required steps such as neutralization, extraction / separation and distillation / collection are significantly reduced in comparison with the conventional methods and therefore a convenient process for producing laurolactam is realized.

[0037]Since solvents suitable for each reaction are also selected as the oxime-formation solvent and rearrangement solvent, the oxime-formation and rearrangement reaction can be completed in a short time, and laurolactam can be obtained in a high yield.

[0038]Since furthermore nonpolar organic solvent stable thermally and chemically is employed for the rearrangement solvent in a preferred embodiment of the present invention, the solvent can be readily collected in a high yield and recycled.

Problems solved by technology

Although laurolactam, which is a starting material for Nylon 12, is also produced in a similar manner, the process is more complex because cyclododecanone oxime as an intermediate product has a high melting point.

This reaction solvent must be able to substantially dissolve cyclododecanone oxime and be inert to concentrated sulfuric acid or oleum, and therefore the selection of the solvent is considerably restricted.

This process does not generate ammonium sulfate as a byproduct in the rearrangement reaction step, but requires enormously large facilities and energy for treating a large amount of waste diluted sulfuric acid.

Furthermore, since cyclododecanone reacts with concentrated sulfuric acid to form a byproduct, the oxime-forming reaction must be completed for eliminating residual cyclododecanone, but due to hydrophobicity of isopropylcyclohexane, a mass transfer rate is low in an oil-water interface, leading to a longer oxime-forming reaction.

As a whole, the process involves many steps of separation, recovery and recycling of solvents and, therefore, requires considerably large equipment expenses and energy.

However, as a process for producing laurolactam, it has the following problems; (1) separation and purification of caprolactam requires large amounts of equipment expenses, resulting in low investment efficiency and the process involves operations of low energy efficiency such as concentration of an aqueous solution of caprolactam; (2) there is a restriction to a production ratio of laurolactam / caprolactam; and (3) caprolactam is a low-value-added product in comparison with laurolactam and an use efficiency of hydroxylamine is low.

Although some of these catalysts and manufacturing processes can provide a high rearrangement yield, these methods employ special catalysts and / or solvents, for which a recovering or recycling procedure is not disclosed, and these are, therefore, unestablished as an industrial process.

However, the solvents used in the rearrangement reaction are polar solvents, specifically, a nitrile which is recommended as a solvent cannot be used for an oxime-forming reaction because it reacts with hydroxylamine to form an amidoxime.

Furthermore, since it is susceptible to hydrolysis, the loss of the catalyst inevitably happens in the step of removing catalyst and the like.

Since it is highly miscible with water, a process for dehydrating materials for rearrangement becomes complex.

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